The Deadline Game: Three Types


deadlineWhether freelancing, or in the corporate world, we all have to contend with deadlines. Deadlines generally come off sounding like shlock horror villains: they inch closer, approach, loom and grow larger. I’ve worked in settings where deadlines were paramount, and followed rigorously, and in situations where they meant surprisingly little.

In this post I’m going to discuss deadline management. Successfully managing deadlines is part knowing why specific deadlines exist in the first place, part knowing which are soft and which are firm, and a big part relationship management. Striking the right balance depends on the situation at hand, but generally speaking, deadlines fall into one of three categories and should be managed accordingly.

First Type: The Faildate

Depending on the institution you’re dealing with, and the level of consultant or employee they’re used to working with, a deadline might actually be a test to see if your work is up to their standards. As a consultant taking on a first contract with a high profile client, for example, a deadline could be the point at which you’re no longer considered for future work. And that’s if you meet them, not exceed them.

To beat these kinds of deadlines, you actually have to beat them. Coming in early is the real key to success, but of course your product can’t suffer as a result. You’ll know when these kinds of deadlines are in play if you do adequate research before signing on with a new client or employer in order to find out about their corporate climate.

Sometimes these types of clients will also want frequent, regular status updates, either weekly or bi-weekly, but even if they don’t, it’s a good idea to micro-manage these deadlines by breaking them down into sub-tasks on a fairly small scale. Hourly goal setting might even be appropriate. Good tools for this kind of work include GTD apps that send you notifications on a schedule you set (Things or Remember the Milk are recommended).

Second Type: Firm, But Flexible

This sounds contradictory, but it isn’t. This will cover the vast majority of deadlines you’ll encounter. These are deadlines that are set as firm, and that should be met if at all possible, but that are susceptible to change depending on circumstances and when in conflict with other deadlines.

The key to successfully negotiating these deadlines is finding out why they exist in the first place. If, for example, a deadline exists for the group you’re working with because without that piece of work, another group is just sitting around waiting, then that deadline takes priority. If it exists because it’s based on a reasonable, pre-project estimate of how much time a task should take, then consider it flexible and move on.

Zen is a nice tool to use to track these kinds of deadlines, because it allows you to create custom groups for your different tasks, so you can make your own priority categories depending on the deadline source.

Third Type: Staledate

The final type of deadline isn’t really a deadline at all. It’s the date at which something ceases to really be a concern, and passes into a client or employer’s distant memory. Be careful, because no one you work for will likely admit that these kinds of deadlines exist, so identifying them won’t be easy.

The best way to go about finding your staledate deadlines is by watching ones from the second category you’ve flagged as low priority. Other signs a deadline may actually indicate when you can drop something entirely include a lack of ability to quantify what would result from meeting said deadline, a lack of client stakeholders associated with it, and lax reporting requirements.

Keep tabs on these as you normally would other dates in your usual PM tools, but don’t worry too much about following through until someone important starts asking questions.

Deadlines don’t have to be the movie monsters we make them out to be. Sometimes they’re just a way of saying “we would like this done within a reasonable period of time,” or even “we don’t care about this at all, but we have to pretend to until time X because the policy says so.” If you listen to your deadlines and monitor them properly, the won’t loom so much as pass uneventfully.

How do you manage deadlines?

Image by Flickr user wili_hybrid.




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Thanks for these. Working for a corp. I get deadlines for tasks and employ agencies to carry out work for me, so I pass down deadlines. The deadlines I pass down are “firm but flexible” as they usually factor in time for amends or changes to the work.

How would you recommend communicating firm but flexible deadlines without making the agency feel that the firm deadline doesn’t really exist?

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